Solvolysis of 1-pent-3-ynyl triflate. Mechanism of the homopropargyl rearrangement

M Hanack, CJ Collins, H Stutz…

Index: Hanack, Michael; Collins, Clair J.; Stutz, H.; Benjamin, Ben M. Journal of the American Chemical Society, 1981 , vol. 103, # 9 p. 2356 - 2360

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Citation Number: 22

Abstract

Abstract: 1-Pent-3-ynyl triflate (lb) was solvolyzed (25 OC, 24 h) in ethanol-water with 2, 6- lutidine as the buffer. Products were formed predominantly (97-98.5%) through direct substitution (k, processes) and elimination. As the water content increases, the yields of 2- methylcyclobutanone (7b)(formed through kA processes) also increase from 0.2%(100% ethanol) to 2.8%(50% ethanol). 1-Pent-3-ynyl triflate was solvolyzed in anhydrous ...